Water → HCID 178510922, compound

HRID 1251179Notes

Reaction equation

HRID 1251179 reaction equation
BrC[C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[C-:10]#[N:11].[Na+].O.C(O[CH2:18][CH3:19])(=O)C>C1(C)C=CC=CC=1>[C:8]([CH2:7][CH2:6][C:5]1[SH:4]([C:10]#[N:11])[CH:3]=[CH:18][CH:19]=1)#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 225036202-(Bromomethyl)thiophene-3-carbonitrile

Product 1

HCID 178510922HCID 178510922, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromomethyl-3-cyanothiophene (2.746 g) was dissolved in toluene (40 ml), followed by the addition of a solution of sodium cyanide (2.002 g)/water (15 ml), and the mixture was stirred at 80° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with an aqueous solution of saturated sodium bicarbonate, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a pale yellow solid (823 mg, yield; 43%).

Workup

  1. washwashed with an aqueous solution of saturated sodium bicarbonate
  2. dry with materialdried (over MgSO4)
  3. customevaporated
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-cd10ed48ad1e4a63bc09b76fa715a435
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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